JP5932338B2 - ジピロメテン−ホウ素親水性蛍光性化合物 - Google Patents
ジピロメテン−ホウ素親水性蛍光性化合物 Download PDFInfo
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- JP5932338B2 JP5932338B2 JP2011542871A JP2011542871A JP5932338B2 JP 5932338 B2 JP5932338 B2 JP 5932338B2 JP 2011542871 A JP2011542871 A JP 2011542871A JP 2011542871 A JP2011542871 A JP 2011542871A JP 5932338 B2 JP5932338 B2 JP 5932338B2
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- 239000007850 fluorescent dye Substances 0.000 title description 10
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- 125000000524 functional group Chemical group 0.000 claims description 23
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- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 6
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- 229910052783 alkali metal Inorganic materials 0.000 description 2
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- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 2
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- 125000000623 heterocyclic group Chemical group 0.000 description 2
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- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
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- 229910052727 yttrium Inorganic materials 0.000 description 2
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 1
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 1
- XVRQXZDZWIBQLJ-UHFFFAOYSA-N CCOP(=O)OCC.OS(=O)(=O)C(F)(F)F Chemical compound CCOP(=O)OCC.OS(=O)(=O)C(F)(F)F XVRQXZDZWIBQLJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QBXVXKRWOVBUDB-GRKNLSHJSA-N ClC=1C(=CC(=C(CN2[C@H](C[C@H](C2)O)C(=O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound ClC=1C(=CC(=C(CN2[C@H](C[C@H](C2)O)C(=O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C QBXVXKRWOVBUDB-GRKNLSHJSA-N 0.000 description 1
- 238000001712 DNA sequencing Methods 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000001503 aryl iodides Chemical class 0.000 description 1
- KVILUFYYUJUTDJ-UHFFFAOYSA-N benzene;n,n-diethylethanamine Chemical compound C1=CC=CC=C1.CCN(CC)CC KVILUFYYUJUTDJ-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- VYXSBFYARXAAKO-WTKGSRSZSA-N chembl402140 Chemical compound Cl.C1=2C=C(C)C(NCC)=CC=2OC2=C\C(=N/CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-WTKGSRSZSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
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- 238000004020 luminiscence type Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- LDYUIVOAQFHBIO-UHFFFAOYSA-N n,n-dimethylprop-1-yn-1-amine Chemical compound CC#CN(C)C LDYUIVOAQFHBIO-UHFFFAOYSA-N 0.000 description 1
- ILBIXZPOMJFOJP-UHFFFAOYSA-N n,n-dimethylprop-2-yn-1-amine Chemical compound CN(C)CC#C ILBIXZPOMJFOJP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000005897 peptide coupling reaction Methods 0.000 description 1
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
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- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0859098 | 2008-12-29 | ||
| FR0859098A FR2940654B1 (fr) | 2008-12-29 | 2008-12-29 | Composes flurorescents hydrophiles a base de dipyrromethenes-bore |
| PCT/FR2009/052606 WO2010076516A1 (fr) | 2008-12-29 | 2009-12-18 | Composés fluorescents hydrophiles à base de dipyrrométhènes-bore |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012513974A JP2012513974A (ja) | 2012-06-21 |
| JP5932338B2 true JP5932338B2 (ja) | 2016-06-08 |
Family
ID=40934068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011542871A Active JP5932338B2 (ja) | 2008-12-29 | 2009-12-18 | ジピロメテン−ホウ素親水性蛍光性化合物 |
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| US (1) | US8476461B2 (fr) |
| EP (1) | EP2382220B1 (fr) |
| JP (1) | JP5932338B2 (fr) |
| CN (1) | CN102300868A (fr) |
| AU (1) | AU2009334646B2 (fr) |
| BR (1) | BRPI0918688C8 (fr) |
| CA (1) | CA2748544C (fr) |
| ES (1) | ES2437614T3 (fr) |
| FR (1) | FR2940654B1 (fr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| FR2940653B1 (fr) * | 2008-12-29 | 2011-02-04 | Centre Nat Rech Scient | Nouveaux composes dipyrromethenes-borosubstitues fluorescents et leur utilisation pour le diagnostic |
| GB201120924D0 (en) * | 2011-12-06 | 2012-01-18 | Johnson Matthey Plc | Tracers and method of marking hydrocarbon liquids |
| FR2993565B1 (fr) | 2012-07-19 | 2016-01-08 | Centre Nat Rech Scient | Composes fluorescents de type thienyldipyrromethene bores et leurs utilisations. |
| CN103666458B (zh) * | 2013-12-16 | 2015-07-15 | 大连理工大学 | 一种用于标记和追踪细胞质膜的荧光探针及其制备方法 |
| KR101598605B1 (ko) * | 2014-01-29 | 2016-03-14 | 한국과학기술원 | 보론 다이피로메텐 화합물 및 이 화합물을 유효성분으로 포함하는 차아염소산 이온 검출용 조성물 |
| US9758625B2 (en) | 2015-03-12 | 2017-09-12 | Becton, Dickinson And Company | Polymeric BODIPY dyes and methods for using the same |
| CN105753892A (zh) * | 2016-03-22 | 2016-07-13 | 天津大学 | 一类具有不同疏水链的水溶性bodipy衍生物及制备方法 |
| US10493153B2 (en) * | 2018-02-01 | 2019-12-03 | Iowa State University Research Foundation, Inc. | Alkylated photoremovable protecting groups and uses thereof |
| JP6867962B2 (ja) * | 2018-02-22 | 2021-05-12 | 富士フイルム株式会社 | 測定対象物質を測定するためのキット、蛍光標識剤および蛍光標識抗体 |
| WO2019191482A1 (fr) | 2018-03-30 | 2019-10-03 | Becton, Dickinson And Company | Colorants polymères hydrosolubles portant des chromophores latéraux |
| US20200048469A1 (en) * | 2018-08-07 | 2020-02-13 | Becton, Dickinson And Company | Polymeric tandem dyes having pendant narrow emission acceptor |
| US11001675B2 (en) | 2018-08-28 | 2021-05-11 | University Of Florida Research Foundation, Inc. | Boronic acid monomers and methods of making boronic acid monomers |
| CN111380842A (zh) * | 2018-12-29 | 2020-07-07 | 复旦大学 | 一种具有aie效应的bodipy类荧光分子及对钯离子的检测方法 |
| FR3101875A1 (fr) * | 2019-10-10 | 2021-04-16 | Centre National De La Recherche Scientifique | Analogue fluorescent de la vancomycine |
| WO2021169661A1 (fr) * | 2020-02-28 | 2021-09-02 | 复旦大学 | Composés bodipy à double substitution cationique en position 4, leurs procédés de préparation et leur utilisation |
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| FR2882056B1 (fr) * | 2005-02-15 | 2007-06-01 | Centre Nat Rech Scient | Dipyrromethenes-bore borocarbones insatures |
| US8003675B2 (en) | 2006-07-12 | 2011-08-23 | Kumiai Chemical Industry Co., Ltd. | 3,4-dihalogenoisothiazole derivative, and agricultural or horticultural plant disease-controlling agent |
| FR2940653B1 (fr) * | 2008-12-29 | 2011-02-04 | Centre Nat Rech Scient | Nouveaux composes dipyrromethenes-borosubstitues fluorescents et leur utilisation pour le diagnostic |
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Also Published As
| Publication number | Publication date |
|---|---|
| FR2940654A1 (fr) | 2010-07-02 |
| BRPI0918688C8 (pt) | 2018-05-29 |
| JP2012513974A (ja) | 2012-06-21 |
| CA2748544C (fr) | 2018-04-03 |
| WO2010076516A1 (fr) | 2010-07-08 |
| CA2748544A1 (fr) | 2010-07-08 |
| IL213818A (en) | 2016-02-29 |
| AU2009334646B2 (en) | 2015-12-10 |
| EP2382220B1 (fr) | 2013-09-04 |
| IL213818A0 (en) | 2011-07-31 |
| FR2940654B1 (fr) | 2012-01-13 |
| EP2382220A1 (fr) | 2011-11-02 |
| BRPI0918688B8 (pt) | 2018-05-15 |
| US8476461B2 (en) | 2013-07-02 |
| AU2009334646A1 (en) | 2011-07-21 |
| ES2437614T3 (es) | 2014-01-13 |
| CN102300868A (zh) | 2011-12-28 |
| BRPI0918688A2 (pt) | 2015-12-01 |
| US20120009615A1 (en) | 2012-01-12 |
| BRPI0918688B1 (pt) | 2018-02-14 |
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